CA2020012C - Un procede pour l'hydrogenation selective d'olefines contenant des groupes nitriles - Google Patents

Un procede pour l'hydrogenation selective d'olefines contenant des groupes nitriles Download PDF

Info

Publication number: CA2020012C
Authority: CA; Canada
Prior art keywords: hydrogenation; selective hydrogenation; nitrile groups; hydrogen; olefins containing
Prior art date: 1989-06-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA002020012A

Other languages

English (en)

Other versions

CA2020012A1 (fr

Inventor

Thomas Himmler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer AG

Original Assignee

Bayer AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1989-06-29

Filing date

1990-06-27

Publication date

2000-06-13

1990-06-27 Application filed by Bayer AG filed Critical Bayer AG

1990-12-30 Publication of CA2020012A1 publication Critical patent/CA2020012A1/fr

2000-06-13 Application granted granted Critical

2000-06-13 Publication of CA2020012C publication Critical patent/CA2020012C/fr

2010-06-27 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 46
150000001336 alkenes Chemical class 0.000 title claims abstract description 13
125000002560 nitrile group Chemical group 0.000 title claims abstract description 9
238000000034 method Methods 0.000 title claims description 24
239000003054 catalyst Substances 0.000 claims description 20
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
150000002576 ketones Chemical class 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 6
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 claims 1
230000003197 catalytic effect Effects 0.000 abstract description 3
150000003303 ruthenium Chemical class 0.000 abstract description 3
-1 tris-(triphenylphosphine)-rhodium(I) halide Chemical class 0.000 description 16
IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 15
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 12
229920001577 copolymer Polymers 0.000 description 9
230000000875 corresponding effect Effects 0.000 description 8
229920000642 polymer Polymers 0.000 description 8
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000004793 Polystyrene Substances 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
229920001971 elastomer Polymers 0.000 description 6
239000003446 ligand Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
229910052703 rhodium Inorganic materials 0.000 description 6
239000010948 rhodium Substances 0.000 description 6
239000005060 rubber Substances 0.000 description 6
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 3
150000001993 dienes Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000178 monomer Substances 0.000 description 3
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
150000001555 benzenes Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
150000002826 nitrites Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
229910052707 ruthenium Inorganic materials 0.000 description 2
229930195734 saturated hydrocarbon Natural products 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
UTAHFAJHGGPJEQ-UHFFFAOYSA-N (2-phenylphenyl)phosphane Chemical compound PC1=CC=CC=C1C1=CC=CC=C1 UTAHFAJHGGPJEQ-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
QFMZQPDHXULLKC-UHFFFAOYSA-N 1,2-bis(diphenylphosphino)ethane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCP(C=1C=CC=CC=1)C1=CC=CC=C1 QFMZQPDHXULLKC-UHFFFAOYSA-N 0.000 description 1
NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
101100298295 Drosophila melanogaster flfl gene Proteins 0.000 description 1
241001441571 Hiodontidae Species 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 description 1
229920000459 Nitrile rubber Polymers 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
DGJOCBJPCSLLKK-UHFFFAOYSA-N bis(2,3-dimethoxyphenyl)-phenylphosphane Chemical class COC1=CC=CC(P(C=2C=CC=CC=2)C=2C(=C(OC)C=CC=2)OC)=C1OC DGJOCBJPCSLLKK-UHFFFAOYSA-N 0.000 description 1
229940074995 bromine Drugs 0.000 description 1
MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
239000001273 butane Substances 0.000 description 1
NQZFAUXPNWSLBI-UHFFFAOYSA-N carbon monoxide;ruthenium Chemical group [Ru].[Ru].[Ru].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] NQZFAUXPNWSLBI-UHFFFAOYSA-N 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
229940018557 citraconic acid Drugs 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
GYBNBQFUPDFFQX-UHFFFAOYSA-N cyclohex-3-ene-1-carbonitrile Chemical compound N#CC1CCC=CC1 GYBNBQFUPDFFQX-UHFFFAOYSA-N 0.000 description 1
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
BOHNWWTZVYEMMA-UHFFFAOYSA-N dibutyl(phenyl)arsane Chemical compound CCCC[As](CCCC)C1=CC=CC=C1 BOHNWWTZVYEMMA-UHFFFAOYSA-N 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
MUBZDQFQOYOFBM-UHFFFAOYSA-N diethyl(phenyl)arsane Chemical compound CC[As](CC)C1=CC=CC=C1 MUBZDQFQOYOFBM-UHFFFAOYSA-N 0.000 description 1
LVTCZSBUROAWTE-UHFFFAOYSA-N diethyl(phenyl)phosphane Chemical compound CCP(CC)C1=CC=CC=C1 LVTCZSBUROAWTE-UHFFFAOYSA-N 0.000 description 1
VPHDWBWBTVPDAZ-UHFFFAOYSA-N diphenyl-(2,3,4-trimethoxyphenyl)phosphane Chemical class COC1=C(OC)C(OC)=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VPHDWBWBTVPDAZ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
125000005670 ethenylalkyl group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000005227 gel permeation chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
229940090044 injection Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052741 iridium Inorganic materials 0.000 description 1
GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
150000002825 nitriles Chemical group 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical class CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
238000010060 peroxide vulcanization Methods 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
VWSSOSUSCXKKKL-UHFFFAOYSA-N phenyl-bis(2,3,4-trimethoxyphenyl)phosphane Chemical class COC1=C(OC)C(OC)=CC=C1P(C=1C(=C(OC)C(OC)=CC=1)OC)C1=CC=CC=C1 VWSSOSUSCXKKKL-UHFFFAOYSA-N 0.000 description 1
OHUBTNCFAYBUKT-UHFFFAOYSA-N phenyl-bis(2,3,4-trimethylphenyl)phosphane Chemical class CC1=C(C)C(C)=CC=C1P(C=1C(=C(C)C(C)=CC=1)C)C1=CC=CC=C1 OHUBTNCFAYBUKT-UHFFFAOYSA-N 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000001294 propane Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
229910052702 rhenium Inorganic materials 0.000 description 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
150000003304 ruthenium compounds Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000010059 sulfur vulcanization Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 1
JRIXTOAARDBEIG-UHFFFAOYSA-N tris(2,3,4-trimethoxyphenyl)phosphane Chemical class COC1=C(OC)C(OC)=CC=C1P(C=1C(=C(OC)C(OC)=CC=1)OC)C1=CC=C(OC)C(OC)=C1OC JRIXTOAARDBEIG-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
125000002348 vinylic group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/04—Reduction, e.g. hydrogenation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

CA002020012A 1989-06-29 1990-06-27 Un procede pour l'hydrogenation selective d'olefines contenant des groupes nitriles Expired - Fee Related CA2020012C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE3921263A DE3921263A1 (de)	1989-06-29	1989-06-29	Verfahren zur selektiven hydrierung nitrilgruppenhaltiger olefine
DEP3921263.7		1989-06-29

Publications (2)

Publication Number	Publication Date
CA2020012A1 CA2020012A1 (fr)	1990-12-30
CA2020012C true CA2020012C (fr)	2000-06-13

Family

ID=6383833

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002020012A Expired - Fee Related CA2020012C (fr)	1989-06-29	1990-06-27	Un procede pour l'hydrogenation selective d'olefines contenant des groupes nitriles

Country Status (5)

Country	Link
US (1)	US5049693A (fr)
EP (1)	EP0405268B1 (fr)
JP (1)	JP2894506B2 (fr)
CA (1)	CA2020012C (fr)
DE (2)	DE3921263A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6060570A (en) *	1996-08-12	2000-05-09	Bp Amoco Corporation	Process for preparation of addition products of difunctional telechelic polyolefins from cyclic olefins by olefin metathesis reaction
GB9816157D0 (en) *	1998-07-25	1998-09-23	Univ St Andrews	Catalyst
US20120029195A1 (en) *	2009-03-31	2012-02-02	Sumitomo Chemical Company, Limited	Method for producing alcohol compound and catalyst therefor
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1989
- 1989-06-29 DE DE3921263A patent/DE3921263A1/de not_active Withdrawn
1990
- 1990-06-16 EP EP90111392A patent/EP0405268B1/fr not_active Expired - Lifetime
- 1990-06-16 DE DE59005412T patent/DE59005412D1/de not_active Expired - Fee Related
- 1990-06-18 US US07/539,570 patent/US5049693A/en not_active Expired - Lifetime
- 1990-06-25 JP JP2164334A patent/JP2894506B2/ja not_active Expired - Fee Related
- 1990-06-27 CA CA002020012A patent/CA2020012C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
DE3921263A1 (de)	1991-01-24
EP0405268B1 (fr)	1994-04-20
JP2894506B2 (ja)	1999-05-24
EP0405268A2 (fr)	1991-01-02
EP0405268A3 (en)	1992-03-18
CA2020012A1 (fr)	1990-12-30
US5049693A (en)	1991-09-17
DE59005412D1 (de)	1994-05-26
JPH0338556A (ja)	1991-02-19

Legal Events

Date	Code	Title	Description
1997-03-21	EEER	Examination request
2007-06-27	MKLA	Lapsed

Publication	Publication Date	Title
US4746707A (en)	1988-05-24	Process for the selective hydrogenation of unsaturated compounds
US4795788A (en)	1989-01-03	Process for the selective hydrogenation of unsaturated polymers containing nitrile groups
US4978771A (en)	1990-12-18	Process for the selective hydrogenation of unsatuated compounds
KR920001317B1 (ko)	1992-02-10	중합체 수소화 방법
JP4607945B2 (ja)	2011-01-05	低分子量ニトリルゴムの調製方法
JPH0426322B2 (fr)	1992-05-07
US20120270996A1 (en)	2012-10-25	Nano-Sized Hydrogenated Diene-Based Latex Particles
EP0601953B1 (fr)	1997-05-14	Procédé pour hydrogéner en solution les double liaisons de polymères de diènes conjugués et des coplymères en block hydrogénés ainsi préparés
KR100267080B1 (ko)	2000-10-02	공액디엔 중합체의 수소화 방법
US5049693A (en)	1991-09-17	Process for the selective hydrogenation of olefins containing nitrile groups
US7385010B2 (en)	2008-06-10	Hydrogenation of diene-based polymer latex
USRE34548E (en)	1994-02-15	Process for the selective hydrogenation of unsaturated compounds
KR101721713B1 (ko)	2017-03-30	불포화된 화합물의 수소화를 위한 촉매
EP1705194A1 (fr)	2006-09-27	Procédé d'hydrogénation des dispersions de latex de polymère conjugués
US7345115B2 (en)	2008-03-18	Organic solvent-free hydrogenation of diene-based polymers
EP1702930B1 (fr)	2010-10-20	Procédé d'hydrogénation des polymères conjugés
KR100250230B1 (ko)	2000-04-01	공역디엔 중합체의 수소화 방법
JPH0686485B2 (ja)	1994-11-02	ルテニウム錯体による重合体水素化法
KR100332464B1 (ko)	2002-11-16	공액디엔 중합체의 선택적 수소화를 위한 촉매 및 이를이용한 수소화 방법
KR100295599B1 (ko)	2001-09-22	공역디엔 중합체의 수소화 방법
KR100221358B1 (ko)	1999-09-15	올레핀성 리빙중합체의 이중결합의 선택적 수소화를 위한 신촉매 제조 및 이를 이용한 수첨 방법
CA2368684A1 (fr)	2002-06-28	Hydrogenation amelioree de l'huile de soja epoxydee